Disclosure: Some of the links below may be affiliate links, meaning, at no cost to you, I will earn a commission if you click through and make a purchase.
Length of stay: 5 nights – 1 in Portland, ME, and 4 aboard the sailing schooner Grace Bailey out of Rockland
Where we stayed: Inn at St. John, Portland, and aboard the Grace Bailey (there are still sailings left with availability in 2023 – book now!)
National park sites visited: 0
National park passport stamps acquired: 0
Why I visited and went sailing in Midcoast Maine
I’ll go into this more in a full trip post, but a few months ago I saw Marc Evan Jackson post about windjamming, sailing on schooner ships out of Maine. He recently became part-owner of one of the boats, and would be aboard some of the trips this summer. My tens of followers *demand* content and this seemed like the kind of interesting content that would resonate. Plus it just seemed different and cool and I’ve been wanting to visit Maine. Hi Friends It’s Julia was game for the trip, so we booked it.
We flew into Portland, ME, although you could also fly into Bangor to reach Rockland. We spent one night in Portland so I could catch up with my friend Jess. Also note you want to fly into Portland International Jetport, PWM, NOT Portland, Oregon PDX.
Highlights of sailing in Midcoast Maine:
Sailing around the Midcoast in the Penobscot Bay on a 141-year-old ship. Meeting interesting new people also sailing on our ship from all walks of life. Meeting Marc Evan Jackson (co-host and co-owner of the Grace Bailey), who you may know from The Good Place, Brooklyn 99, The Babysitter’s Club, etc. He is as delightful and cool and normal as one would hope. Eating our weight in seafood, desserts, and drinks. Played with Fiji the cat!
Sparkle Pony is a great name for a band AND an adult beverage 
Fiji the cat rules the boat
A final highlight was discovering Maine Craft Distilling’s Sparkle Pony beverage and also Old Bay Goldfish. We went to like SIX Hannaford’s to find them again and couldn’t. My life needs these!
Lowlights:
Our Portland hotel room was up three flights of stairs with no elevator. It was also NOT in the heart of Portland like I thought it was. That’s oh-for-two on recent hotel stays for HFIL (Columbia, SC, was the other fail). We also overpacked for the boat, making our small room even more cramped. I slept with my tote bag by my pillow and bookbag on the end of my bed for space.
Note all of the luggage we took to our third floor hotel room 
and note the tiiiiiny bunk filled with luggage
What we did sailing in Midcoast Maine:
Met up with my friend Jess in Portland, where she is staying for the summer. We ate lunch at Portland Lobster Co and walked around the waterfront area which had many cute shops. I resisted purchasing anything. That’s a lie. I bought some cute little stuff but resisted purchasing a SeaBag tote or an entirely new kitchen set. I would like an award for showing such restraint, please.
Aboard the GB, we sailed around the Gulf of Maine, rafted up with other schooners in the Maine Windjammer Association, ate lobster, and drank a custom cocktail the Gamtastic Schooner GamSlam (trademark pending). I took the row boat out one day after a few GamSlams and was still pretty good at it. Not to brag or anything (💅).
Our sail on Grace Bailey was about four days and nights, although she sails anywhere from three nights to six. If that’s just too long for you, or if you have littles, or want something shorter you can sail out of Camden or Rockland on afternoon trips.
What we didn’t do:
Any walking tours, food tours, museum tours, or kayaking. I thought we would have time Saturday morning but our morning was filled with errands to prep for getting on the ship. I ended up buying the Patagucci Duffel bag I’ve wanted for ages to take on the boat. No affiliate link; you know how to shop online.
Approximate trip cost (for one-ish) for sailing in Midcoast Maine:
Airfare: $860
Hotel: $394 total (YIKES – this was NOT a four hundred dollar hotel. It didn’t even have an elevator)
Grace Bailey: $1250
GB Tip: $125
Rental Car: $543
Food: $350
Gas: $40
Entrance fees: $0
Total = $2982
The food is approximate – I paid for some of my sister’s meals, the booze, and treated a dinner for my friend and her boyfriend. I’m surprised looking back how expensive the hotel was. We picked it because it had two queen beds, free parking and free breakfast. The breakfast area was so tiny it was hard to scoot by other people for it. The folks there were super nice though! Were I to visit again, I would stay out in the sticks to save some money.
I also tried Capital One Travel this time for the Portland hotel and the return portion of my flight. I had no problems at all with the booking or noticed anything different from booking direct with American Air for my flight, and still received my airline miles on Alaska as a partner booking. I would recommend the Capital One Venture or Venture X card to accumulate miles. (Affiliate link, if you are approved, I will receive some miles.)
Books I read:
Longtime fans (all three of them) know I love to read books about where I travel. This trip included a lot of cozy mysteries.
- The Secret Life of Lobsters: How Fishermen and Scientists are Unraveling the Mysteries of Our Favorite Crustaceans by Trevor Corson – I loved this book! It’s a lot like Cod, which was one of my favorite books of last year.
- Maine Clambake Mystery series Books 2-4 by Barbara Ross – Classic cozy mystery series set in a sort-of-Rockland town
- Vacationland by Meg Mitchell Moore – women’s literature story set in Rockland. Fun to recognize a lot of the local restaurants while we were there
- Twisted Threads (Mainely Needlepoint Book 1) by Lea Wait – this was fine.
- Evvie Drake Starts Over by Linda Holmes – OK I read this when it came out a few years ago, but it’s set in the Midcoast and I loved it. Loved it!!!!
- All links are affiliate links to Bookshop.org, which supports independent bookstores and not the big Bezos ship
📍I acknowledge that Maine is on indigenous land of the Abenaki, as well as the sovereign people of the Wabanaki Confederacy: the Penobscot, Passamaquoddy, Maliseet and Mi’kmaq peoples.
Check out MY GUIDE TO HAWAII VOLCANOES NATIONAL PARK. Want to read more about my LOVE OF NATIONAL PARKS ? all of my Parks posts are here.
